Editor’s note: the previous edition had a typo. It has now been corrected.

I am at Stripe Sessions in San Francisco this week, and it has been fascinating to watch. The things I have been writing about for years, fintech infrastructure, payments, the future of commerce, are converging in real time on one stage. The lines between financial services, ecommerce, and experiential spending are dissolving fast.

Which is exactly what I want to talk about this week.

Before I flew out here, my friend ran the Brooklyn Half Marathon on Sunday. On Saturday I helped her pick up her race packet. That is all I planned to do. Walk in, get the bib, walk out.

Instead I spent two hours inside one of the most deliberately engineered spending environments I have encountered in a long time. And I was not even the one racing. Brooks had a treadmill on the floor with a purchase incentive if you tested a pair on the spot. Not a discount code to use later. A transaction, right there. A recovery brand's sample station ended in a QR code that went directly to subscription checkout. There was hype music playing the entire time, and I watched people make purchase decisions visibly faster when the right song came on.

Nobody was studying it. It was just working.

Here is what I took away.

Race expos, team stores, pregame plazas. These are not amenities. They are high-intent purchase environments filled with people who have already made one commitment and are neurologically primed to make more.

Behavioral economists call this "goal contagion,” that is, when a person has activated a meaningful personal goal, their willingness to spend on anything adjacent to that goal increases significantly. The race expo is goal contagion at scale.

The global sports event industry is worth over $600 billion and growing. But the monetization of the hours immediately surrounding the event, the window between arrival and competition, remains largely amateur. Most brands show up with a banner and a bag of branded pens. The ones doing it right are building point-of-sale infrastructure into the physical experience itself. The ones doing it wrong are handing out QR codes that go to a homepage.

The opportunity is not in the event. It is in the twenty-four hours on either side of it. That window is underbuilt, underpriced, and wide open.

I watched people make purchase decisions faster when the right song came on.

Music at live events is not ambiance; it is a conversion mechanism. The right song at the right moment does something to a crowd that no banner ad, no re-targeting pixel, no sponsored post will ever replicate. Brands paying for sonic presence at live events are not buying impressions. They are buying a physiological state in a captive, emotionally elevated audience. That is a different category of attention entirely, and it is still being priced like a line item in a sponsorship deck.

The live music industry crossed $31 billion in revenue in 2023 and is still growing post-pandemic. But the infrastructure connecting music performance to real-time transactions is almost nonexistent. Tip-enabled live audio, synchronized crowd payment moments, playlist-as-loyalty-mechanic: none of this is built at scale. What Spotify built for the couch, someone is going to build for the crowd. The payment layer underneath that is wide open.

The global wearable payments market is still early but accelerating fast. NFC-enabled wearables, smart rings, and event-specific payment bib technology are converging on a consumer population that is already comfortable with contactless and actively resistant to pulling out a phone in physical contexts. The use case that cracks this wide open is not the everyday commute. It is the outdoor, athletic, experiential moment. That is where behavior is changing first, and that is where the infrastructure needs to catch up.

Any founder building payments for physical, mobile, outdoor contexts needs to be thinking seriously about form factor right now. The phone is not the default in these environments. It is the fallback.

The brands that showed up as a logo on a banner did nothing. I walked past ten of them and I cannot tell you a single name. The brands that put a treadmill on the floor and a purchase incentive at the end of it closed deals. The brands whose samples came with a checkout link rather than a brochure had lines.

This is not a new observation, but it is one the industry is still failing to act on at scale. Traditional sports sponsorship is built on reach metrics: eyeballs, impressions, brand recall. The experiential model runs on a completely different logic. You are not trying to be remembered. You are trying to be embedded in a transaction. You are trying to own the moment when someone decides to spend, not the moment when they decide to pay attention.

The brands executing this well are not the biggest spenders. They are the ones who understand that the event is a distribution channel, not a billboard. The shift from visibility to transaction ownership is already happening. The measurement frameworks to prove its ROI are still being built, which is exactly where I would be looking if I were investing in sports marketing infrastructure right now.

Every person in that expo was going to post about the race. They were going to tag brands, share their splits, document the whole experience across Instagram, Strava, TikTok, and whatever group chat was running their training accountability. The smartest sponsors in the room were not trying to reach the runners as consumers. They were turning the runners into the campaign.

This is the creator economy applied to mass participation sports, and it is much bigger than most people realize. A 27,000-person half marathon is not just a race. It is a content production event. Every finisher photo is a brand placement opportunity. Every Strava upload is a data point. Every post-race Instagram story is earned media. The brands that have figured out how to be in that content organically, not through a watermark or a sponsored tag, but through actually being part of the experience, are winning in a way that is essentially impossible to buy through traditional media.

The infrastructure to enable this at scale, the tools that let brands identify, activate, and measure athlete-creators across mass participation events, is being built right now. It is one of the more interesting spaces I am watching heading into the back half of 2025.

This is the list I keep in my back pocket. Not the names getting press. The ones building the infrastructure I described above: wearable payments, live event monetization, athlete creator tools, experiential activation platforms, and the fintech rails underneath all of it.

Goes out to paid subscribers only. If you have been thinking about upgrading, this is the week.

If you want to get in front of an engaged audience of founders, operators, and investors, I'd love to hear from you.

Bear and the Bull is at 1,200+ subscribers and a 60% open rate - well above industry averages. 2/3 of readers are in fintech, 40% are founders. These are decision-makers who actually read.

Reach out to [email protected] for partnership options.

I’ll be mostly in LA next week with a detour to San Diego. Email me if you’d like to grab coffee!

San Diego | May 5 | I’ll be attending a dinner for fintech investors & founders.

🎧New Money Memories will be airing soon, featuring founders I met during my New Orleans trip. I’ve been doing more in-person recordings, and excited to share more about the exciting guests I have in store!

👉 Listen on NPR, Apple, Spotify, or wherever you listen to podcasts

📌How Silicon Valley’s Brightest Parents Broke Their Own School

📌 The $13 bln World Cup

If you find this valuable, here are a few ways to support Bear and the Bull (most of which are free):

Wispr Flow recognizes variable names, file references, and framework syntax mid-dictation. Speak your prompt, get developer-ready text for GitHub, Jira, or your editor. No mangled syntax. Ever.

Try Wispr Flow free

Till next week,
Ilona